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5 on this page| № | Name | Category | Address | Record |
|---|---|---|---|---|
| 01 | Middleton A women's clothing and lifestyle boutique on Main Street, opened 2022, curating quality-over-quantity apparel brands. | Boutique | 66 Main StMiddlebury, VTMiddlebury Village Historic District | Listed · independent · address on record |
| 02 | Vermont Book Shop An independent bookstore continuously operating since 1949, a Main Street literary landmark for Addison County. | Bookstore | 38 Main StMiddlebury, VTMiddlebury Village Historic District | Listed · independent · address on record |
| 03 | Otter Creek Bakery A European-style bakery and deli operating since 1986, known for scratch-made breads, pastries, and gourmet sandwiches. | Bakery | 14 College StMiddlebury, VTMiddlebury Village Historic District | Listed · independent · address on record |
| 04 | Royal Oak Coffee A small specialty coffee shop serving espresso drinks and baked goods in a cozy downtown setting. | Coffee Shop | 30 Seymour StMiddlebury, VTMiddlebury Village Historic District | Listed · independent · address on record |
| 05 | Mister Up's Restaurant & Pub A casual American restaurant and pub on Otter Creek, a Middlebury dining staple since the 1970s known for its riverside deck. | Restaurant | 25 Bakery LnMiddlebury, VTMiddlebury Village Historic District | Listed · independent · address on record |